US2111820A - Alkyl aromatic acetic acid and homologues thereof - Google Patents

Alkyl aromatic acetic acid and homologues thereof Download PDF

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Publication number
US2111820A
US2111820A US53674A US5367435A US2111820A US 2111820 A US2111820 A US 2111820A US 53674 A US53674 A US 53674A US 5367435 A US5367435 A US 5367435A US 2111820 A US2111820 A US 2111820A
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Prior art keywords
acid
parts
product
water
instance
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US53674A
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English (en)
Inventor
Steindorff Adolf
Platz Carl
Rosenbach Johann
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IG Farbenindustrie AG
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IG Farbenindustrie AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
    • C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
    • C07C33/20—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part monocyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/03—Organic sulfoxy compound containing
    • Y10S516/05—Organic amine, amide, or n-base containing
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/06—Protein or carboxylic compound containing

Definitions

  • the present invention relates to alkylation products of aromatic acetic acid and homologues thereof.
  • alkyl groups may be introduced in a smooth reaction and with good yields into monoor poly-nuclear aromatic compounds containing an aliphatic substituent to which at least one hydrophilic group is linked.
  • the condensation of the alcohols or oleflnes takes place mainly in the aromatic nucleus.
  • butylated phenylacetic acids are formed.
  • the process may' also be performed, for instance, by treating ben-
  • the smooth introduction of the alkyl groups into zyl alcohol with 3 mols of ethylene oxide and al- 10 the said compounds is surprising, It is particuky at n e o o-ben yl ether of trig y larly remarkable that several alkyl radicals may t e formu a: be introduced with ease into the aforesaid aromatic compounds containing an aliphatic radical, @cmcwmcnohcmcmon to which at least one hydrophilic group is linked since as is known the manufacture of hi her 15 8 thus formed, or the naphthylacetic acid may be alkylated products from, for instance, benzene transformed mm the ms h 1
  • exy nap hy ace 0 As monoor poly-nuclear bodies, containing 28 3: g with isohexyl alcohol and aliphatic substituents to which at least one hy- 2 drophilic group is linked, there may be used, for t g f fi ij fi rw correspond;
  • phenyl acetic o o ow g genera orm acid ethylphenyiacetic acid, alpha-phenylbutyric (R1) 3 1; acid, hydrocinnamic acid, naphthylacetic acid, acenaphthenylacetic acid, phenylethylalcohol, wherein A stands an aromatic g system,
  • R2 means an aliphatic radical and wherein cmo omon,o ,omomon x stands for a hydrophilic group, for
  • hydrophilic' groups there may therefore be substituted named, for instance, the following: -OH,' for instance, di-, triand tetrabutylphenylacetic -COOH, -NH-.- or monoor (ii-substituted acid, tetrabutylnaphthylaceticacid, di-isohexylamino groups or a quaternary ammonium group, hydrocinnamic acid, di-isopropylnaphthylacetic 35 a polyglycol or polyglycerol radical. acid, insofar as they contain acid or basic groups,
  • aliphatic radicals to be introduced into the may be transformed into sa s r t y be aforesaid aromatic compounds, which radicals sulfonated by a treatment with sulfuric acid. may "be substituted or interrupted by hetero-
  • the products are particularly valuable as they 40 atoms, there may be named, for instance: ethyl-f have proper ies of cap v y- T y are 40 propyl-,- isopropyl-, butyl-, isobutyl-, isohexyl-, distinguished by a high wetting and emulsifying lauryl-, tertiary butyl-, chlorohexyl-, oxybuty1-, action.
  • the following compounds, for instance, for washing white goods, in the textile industry are adapted for the alkylation of the above menf r washin 10059 W for Wa hing piece goods.
  • tioned bodies propyl-, butyl-; hexyl-, lauryl-, Some of them, particularly those which contain stearyl-, isobutyl alcohols, monobutylglycol or sulfo-, ester-Sulf acid, 1 polys h the olefines corresponding to these alcohols such radicals, have high stability in presence of acids, 50 as, for instance, propylene, isobutylene, dodecalkalies and salts that cause the hardness of ylene, furthermore their halogen substitution water, so that they may be used with advantage, Products. for instance, in dye-baths, in carbonizing baths As condensing agents there may be used: sulor in kier-boiling. v The products may be used either alone or in 55 furic acid monohydrate, dilute sulfuric acid,
  • condensation may also be performed with isohexylalcohol.
  • tetrabutylhydrocinnamic acid By using larger quantities of n-butylalcohol and sulfuric acid monohydrate higher butylated hydrocinnamic acids, for instance, the tetrabutylhydrocinnamic acid, may be obtained.
  • delta-phenyl-n-valerianic acid (obtainable by condensing cinnamic aldehyde with malonic acid, hydrogenating and decarboxylating) are dissolved in 560 parts of n-butanol and, at 50 C. to 60 C., 1040 parts of sulfuric acid monohydrate are added in the course of one hour. The whole is then'stirred for 15 hours at 65 C., then poured on ice, worked up in the usual manner and sapcnifled.
  • the butylated delta-phenyl-n-valer ianic acid obtained has the acid number of 156.0 and a saponiflcation number of 170.2
  • the product obtained in the form. of a brown powdery mass.
  • the product is distinguished by a good wetting and forming action.
  • Sodium polybutylnaphthylacetate obtainable according to Example 3, is suitable for use as a hot wetting agent.
  • a wetting duration of 2 minutes according to the floating test (1. e. the wood floats for 2 minutes before it sinks in the liquid)
  • 0.03 gram of the aforesaid product is necessary per liter of washing liquor.
  • the reaction product is poured on to ice, washed with a sodium chloridesolution and neutralized.
  • the sodium salt dissolves very easily in water and forms strongly frothing solutions of high wetting action. It probably has the following compositions:
  • a wetting agent is the following constitution:
  • the tri-isobutylphenylacetic acid ethanolamide obtained is adapted for stabilizing emulsions.
  • reaction product obtained which corresponds to the following formula I DCH:.CH:.C ON-CHs-CHpOSOsNI Co n and dissolves in water to a clear solution. is rendered feebly alkaline to litmus paper by means of caustic soda solution.
  • a product for cleansing household linen is obtained by causing 2 mols of dodeoylene to react upon 1 mol. of phenylacetic acid in the presence of borontrifluoride, as described in Example 6.
  • the alkali salts of this condensation product dissolve in water and yield strongly foaming solutions of good washing power.
  • ethylene oxide products which are extraordinarily soluble in water and may be used as dispersing agent, for instance, for calcium soap or pigments.
  • An agent for emulsifying for instance, for neutral oils such as castor oil is obtained by oxethylating tri-isobutylphenylacetic acid with 15 mols of ethylene oxide. 5-10 parts of this product are mixed with 90-95 parts of olive oil. A good emulsion is obtained by pouring the mixture obtained into water. Other oils such as, for instance. turpentine oil or mineral oils may well be emulsified in a similar manner. For the emulsiflcation of oleine it is of advantage to use an oxethylation product contaimng 20 mols of ethylene oxide.
  • R1 stands for an aromatic hydrocarbon radical or at; least 3 carbon atoms, n means a whole number higher than 1, R: means an allphatic hydrocarbon radical, the products in the form of their water-soluble compounds'having capillary activity.
  • A stands for an aromatic hydrocarbon radical.
  • R1 stands for an aliphatic hydrocarbon radical of at least 3 carbon atoms, 11. means a whole number higher than 1, the products in the form of their water-soluble compounds having capillary activity.
  • R1 stands for an aliphatic hydrocarbon radical of at least 3 carbon atoms, 11. means a whole number higher than 1, the products in the form of their water-soluble compounds having capillary activity.
  • n stands for a whole number higher than 1, the products in the form of their water-soluble compounds having capillary activity.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
US53674A 1934-12-08 1935-12-09 Alkyl aromatic acetic acid and homologues thereof Expired - Lifetime US2111820A (en)

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DE2111820X 1934-12-08

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US (1) US2111820A (fr)
FR (1) FR798970A (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2444869A (en) * 1945-04-27 1948-07-06 Us Rubber Co Manufacture of sponge rubber
US2463942A (en) * 1945-08-24 1949-03-08 Lilly Co Eli N-phenylacetylated amino alcohols and ethers
US3168569A (en) * 1960-02-01 1965-02-02 Mo Och Domsjoe Ab Method of bleaching polyalkylene ethers
US3959460A (en) * 1967-08-07 1976-05-25 L'oreal Cosmetic compositions containing anionic surface active agent containing mono- or polyhydroxylated mono- or poly ether chains and a terminal acid group

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2444869A (en) * 1945-04-27 1948-07-06 Us Rubber Co Manufacture of sponge rubber
US2463942A (en) * 1945-08-24 1949-03-08 Lilly Co Eli N-phenylacetylated amino alcohols and ethers
US3168569A (en) * 1960-02-01 1965-02-02 Mo Och Domsjoe Ab Method of bleaching polyalkylene ethers
US3959460A (en) * 1967-08-07 1976-05-25 L'oreal Cosmetic compositions containing anionic surface active agent containing mono- or polyhydroxylated mono- or poly ether chains and a terminal acid group

Also Published As

Publication number Publication date
FR798970A (fr) 1936-05-29

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